Propyl p-toluenesulfonate → HCID 86623293, compound
Reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:10][CH:9]([NH2:11])[CH2:8][CH2:7][C:5]=2[N:6]=1.[S:12]([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)([O:15][CH2:16][CH2:17][CH3:18])(=[O:14])=[O:13]>C(O)CC>[CH3:16][CH2:17][CH2:18][NH:11][C@@H:9]1[CH2:10][C:4]2[S:3][C:2]([NH2:1])=[N:6][C:5]=2[CH2:7][CH2:8]1.[CH3:23][C:22]1[CH:24]=[CH:25][C:19]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:20][CH:21]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
A 250 ml, three necked flask was equipped with a magnetic stirrer, a temperature probe, a heating mantle, a claisen joint, a reflux condenser, and a 100 ml addition funnel. The flask was charged with 5 grams of racemic 2,6 diamino-4,5,6,7-tetrahydro-benzothiazole, followed by 80 ml of n-propanol. Under continuous stirring, the mixture was heated to a temperature of 95° C. over 15 minutes generating a clear solution. The addition funnel was charged with a solution of 10.12 grams propyl tosylate and 9.2 ml diisopropylethyleamine in 28 ml n-propanol. This solution was added dropwise to the 250 ml flask with continuous stirring over a period of 2 hours. The reaction was continued with stirring for an additional 6 hours at 95° C., after which the solution was brought to room temperature, and stirring was continued for an additional 6 hours.
Workup
- customA 250 ml, three necked flask was equipped with a magnetic stirrer
- additiona temperature probe, a heating mantle, a claisen joint, a reflux condenser, and a 100 ml addition funnel
- additionThis solution was added dropwise to the 250 ml flask
- stirringwith stirring for an additional 6 hours at 95° C.
- customwas brought to room temperature
- stirringstirring
- waitwas continued for an additional 6 hours
Sources & evidence
- ORD record
- ord-48ea41d31baf4e749dd36563dcbcfec9
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524695B2
Reaction notes
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